


Just Like Dean

by AnnaNocturnal



Series: Requests and Challenges [3]
Category: Supernatural
Genre: Dildos, Double Penetration, F/M, PWP, Voyeur Sam, Voyeurism, porn stars, toys kink
Language: English
Status: Completed
Published: 2015-04-04
Updated: 2015-04-04
Packaged: 2018-03-21 04:48:30
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 7,720
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3678162
Author URL: https://archiveofourown.org/users/AnnaNocturnal/pseuds/AnnaNocturnal
Summary: <blockquote class="userstuff">
              <p>One of Sam's favorite things about Jess is her filthy mouth. When she tells him about her favorite dildo, he doesn't recognize the porn star that it's modeled after, but he's more than willing to spend some...quality time with her that night, using it. </p><p>The next day, Jess meets Dean when he comes to dinner at their apartment. She recognizes him instantly as Daniel Wesson, but she manages to make it through the world's most awkward dinner without spilling the beans. </p><p>But now Jess is curious...can't stop fantasizing about being fucked by her favorite porn star as her boyfriend watches. Can she get Sam on board with the idea?</p>
            </blockquote>





	1. Part One

**Author's Note:**

> Written for [this prompt](http://spnkink-meme.livejournal.com/94674.html?thread=36874962#t36874962) at the spnkink-meme livejournal community.

One of the things that had first attracted Sam Winchester to Jessica Moore had been her blunt way of speaking. The woman had a complete lack of shame, in the appropriate setting, and once Sam had discovered that, he couldn’t get enough of it. It was something of a comfort zone for him, being told things that would make the average person uncomfortable. He guessed it probably had something to do with growing up with only his dad and older brother, in a household where it wasn’t really all that weird to hear someone beating off without apparent care to who might hear or to walk into the kitchen to hear someone discussing the previous night’s events over cereal or eggs. Sex was a fact of life, and the dirty details of it made for as comfortable conversation for Sam as the weather or a good book.

But there was something about those filthy words and details slipping from a girl’s soft lips— _his_ girl’s, _his_ Jess’ soft, pouty lips—that had him ready to go in a way that his father and brother had _never_ managed with their stories.

And the fucking dichotomy of it; when they were out in public or around friends and Jess was the perfect picture of demure and chaste, until they get back home, alone, and then she’s telling him all sorts of dirty shit. Shit she wants him to do to her, shit other guys have done to her, _shit other girls had done to her_ —those were especially nice—and hell, even shit she’d done to herself.

“So we’re in that horrible, overly-warm lecture hall listening to Dr. Pettit drone on and on…” Jess rolls her shoulders as though just the memory were boring her to tension. “And I’m about to lose my ever-loving mind and I look over at you and _of course_ you’re hanging on the guy’s every word, with that serious face on—”

“You love my serious face.” Sam took the seat beside her on the couch, angling his body towards her, one long leg stretched out behind her before leaning forward to pull her around and against him, her back to his chest, and then bringing up his other leg to trap her between them. He starts rubbing her shoulders, working out the tension and she lets out a soft moan.

“I do,” she conceded, and Sam could practically hear the wicked smile. “It’s almost exactly like the face you make when you’re about to come. Not _quite_ there, that’s an entirely different one, but when you can feel it building up, when it first catches your attention.” She paused to take a sip of her wine. “Anyway, it got me thinking, ‘cause as I said, orgasm-face.”

“Yeah?” Sam egged her on, wanting to hear the rest of the story spill from her lips, knowing it went somewhere good—they always did.

Jess moaned as he hit an especially tight spot between her shoulder and neck. “Mm-hmm. So I’m sitting there thinking about you, and what we could do to put that look back on your face in a much more enjoyable way than listening to one of Dr. Pettit’s lectures, and I realize that it’s my last class but you have three more because of your stupid overloaded schedule. And I’m sure even my vagina can’t drag you away from class. Driven bastard.” Her tone was teasing, but Sam was sure that was the point—teasing him with what he had missed.

“Well, I went to all my classes, so clearly you abandoned that idea.” He couldn’t decide if he _would_ have missed class or not. Probably not, if he was honest. Jess knew him well. “So what did you do instead?”

Jess shrugged, playing nonchalant. “What could I do?” She set her wine glass on the coffee table and turned around, climbing to her hands and knees between Sam’s legs and bringing her face close to his, nearly whispering in his ear. “I was _so wet_ , Sam. So ready for you.” She dodged as Sam growled and tried to capture her lips, giggling. “Needed it _so bad_. So I fucked myself, right here. Screamed your name as I came. Neighbors probably thought you were home.”

“ _God, Jess_ ,” Sam groaned, his hands gripping her at her sides and pulling her forward, forcing her to straddle his lap for balance as he claimed her lips. Her hot core swept over his cock and he let out a broken curse, thrusting up towards her. “You’re such a _slut_. _My_ slut. I can just see you here, see your face as you fuck your own fingers, screaming my name.”

She gasped, the friction of Sam’s hard dick through her panties and sleep shorts making her writhe, seeking out more. “Not…not my fingers.”

And Sam had to concentrate hard to stop himself from creaming his pants like a teenager when images of Jess fucking herself with any number of possible toys filled his head. “The purple one?” he choked out, trying to complete the mental picture.

“Mmm, no…” Jess seemed distracted, less interested now in talking. “This one’s made from a cast of Daniel Wesson’s dick.”

That gave Sam pause as his mind flipped through a catalogue of people he knew—including Jess’ exes, because fuck, there had to be a line somewhere, right? “Who?”

“Porn star,” Jess explained shortly before leaning in to lick a teasing line from Sam’s ear to his collar. “My favorite one.”

“Go get it.” It was a spur-of-the-moment command, and Sam wasn’t sure where it came from. He and Jess didn’t often incorporate toys in their sex acts, other than the occasional costume or fuzzy handcuffs. Right then all he knew was that he needed to see her do it, just like she had described. “Wanna watch you fuck yourself.”

She flushed a light pink, the closest to embarrassed that Sam had ever seen her, but hurriedly climbed off of him and headed for the bedroom. Sam picked up her forgotten wine glass and tossed back the contents as he heard a drawer open and then slam shut a few seconds later. He looked up when he heard her come back into the living room and held out his hand.

She smiled slyly and handed over the flesh-colored silicon dick. “You’re bigger,” she purred, and while that hadn’t been Sam’s concern—he had plenty to be confident about, and he knew it—he still felt a slight swell of pride in his chest.

And really, it was saying something. The fake dick was long, nearly eight inches, and thick enough that his fingers barely touched around it. He smirked and handed it back to her, settling into the couch once more. He gave her a pointed look and nodded at the other end of the couch as if to say, _Get to it_.

Jess bit her lip coyly and sat on the opposite end of the couch, her back supported by the arm, one leg bent and leaning against the back cushions, the other dangling loosely over the side. She winked at him as he crawled towards her and hooked his fingers through the waistband of her shorts and the lace of her panties and pulled, exposing her in one sweeping motion. She gasped at the feel of cool air on her soaked center, her head falling back for a moment as Sam licked his lips. He could barely resist the sight, her smell. He wanted to bury his face between her legs, eat her pussy until her hands were tangling in his hair to hold him still while she fucked his face, rubbing her juices all over him.

But more than that, he reminded himself, he wanted to watch her get herself off on that porn star’s dick. _Daniel Wesson_. Sam had never heard of him but hey, thanks man, for making this moment possible.

So Sam just smirked and leaned back, watching expectantly as Jess pouted, knowing full well what he had been considering doing.

One of her hands came up and then slid between her legs, two fingers slipping through the soaked folds to tease at her clit. She let out a soft sigh and Sam shifted, resisting the urge he felt any time she made noises like that to just fucking take her.

She didn’t stop rubbing her clit as she brought the toy to her quivering entrance, sliding it through her wetness, teasing herself and Sam, whose eyes had darkened as he watched her. She met those dark eyes, holding his gaze, and pushed the dildo in, letting out a hoarse cry as it filled her, stretched her pussy wide for Sam’s eyes.

Sam brought his hand to his still-covered dick, pushing against it to stop from coming at the sight of Jess quickly fucking herself with the fake dick. Her back arched off the arm rest, her hips thrusting slightly as she pulled the toy out and pushed it back in, her rhythm quick and punishing. He could tell by the cries that she was going to come, and soon, and fuck if he wasn’t going to have some part of it.

He leaned forward, climbing onto his hands and knees and moving to Jess. He swatted her hands away and grabbed her hips, guiding her to her hands and knees before settling down behind her, watching the dildo move slightly with her erratic breathing and the fluttering of the muscles deep inside of her. He reached out, closed his hand around the end of the toy and slid it, slowly, out and back in. Jess let out a tormented moan and her head dropped to hang between her shoulders, her fingers curling into the upholstery of the couch.

“So fucking hot. So _wet_.” Sam was just babbling at this point, speaking any thought that entered his mind. “You wanna come, Jess? Wanna come on this fake dick? That what you want, baby?”

“Please, Sam.” Jess’ voice sounded completely wrecked, desperate and needy. “Anything, baby. Anything. Just make me come.”

“Anything?” Sam grinned wickedly. “What if I shoved this deep in your ass; fucked your tight little pussy myself?”

He saw Jess quiver around the dildo as she tossed her head back, a desperate cry issuing from her throat. “Please, Sam.”

“You like that? Like the idea of two dicks in you? You’re practically squirting at the thought.” And Sam considered it, he really did, especially when Jess screamed, half in ecstasy, half in frustration. But… “Maybe another time, baby.”

He pulled the dildo out, making a soft comforting noise when Jess cursed loudly, the end sounding more like a sob than anything, and then raised up to kneel behind her, sliding his pajama pants down to pool at his knees before slamming into her, hard.

“ _God, Sam_!” She was screaming now, and Sam couldn’t help but smile at the thought that everyone on their floor could probably hear her; could hear her getting well and thoroughly fucked by him. “Fuck me! Harder, Sam! I need it so fucking bad!”

“ _Fuck_.” Sam pushed into her deeper, faster, his thrusts becoming almost punishing. “Fuck, you feel so fucking good, Jess. Come for me, baby. Come on my dick.”

She did, a few thrusts later, her juices flowing freely and soaking his dick and groin. Sam gave a few more sharp thrusts and followed, his vision whiting out for a moment as he spilled inside of her.

Afterward they lay panting, their limbs tangled together to the point that it was hard to tell where one of them ended and the other began, a layer of sweat cooling on each of them.

“See, Sam?” Jess breathed out with a small laugh. “It pays off to go to class like a good boy.”

Sam laughed and slowly detangled them to pull her up to rest against his chest, his fingers petting softly at her wild blonde hair. She pressed a kiss to his chest. “Speaking of which, what time should I expect you two tomorrow? Just after your last class or…”

Sam furrowed his brow, trying to recall what she was talking about. “What?”

“I can’t believe you forgot.” Jess laughed, shaking her head. “Dean’s coming for dinner, remember?”

Sam shrugged. Like he was thinking of his brother at a time like _this_.

“Yeah. We should be here around five.”


	2. Part Two

Jess had managed, through some act of god, to swing a Tuesday/Thursday schedule for the current semester, which meant that, though those days were heavily-loaded with classes (no matter how much she teased Sam, her classes just started earlier and ended earlier than his and they both knew it), she had her Mondays, Wednesdays, and Fridays free. Which, this week, meant that she had plenty of time to stress about Dean Winchester’s steadily-approaching visit.

Jess didn’t know a whole lot about about Sam’s family; just the basics, really. She knew that his mom had died in a fire when he was a baby, and that Sam had grown up with his brother and father. She knew that they moved around a lot, and that Sam hated always being the weird new kid in each new town they came to. She knew that John and Sam had some sort of falling out when Sam decided to go away to college, and she knew that John had cut Sam off financially. And because she knew this, she knew that it was actually Dean who was footing the bill for Sam to attend Stanford.

But past that, she was out. She didn’t even know what Dean looked like, although she imagined him as an older, taller (as ridiculous as that was), more serious Sam. And all of that added up to one intimidating motherfucker. Not that Jess was one to really get intimidated by anyone; it was still enough to make her nervous about his arrival, though.

She spent her day flitting around the apartment, cleaning and tidying, then re-tidying, fluffing pillows and rearranging the items on the coffee table until she thought she was going to drive herself crazy. Finally, around two o’clock, she left to go to the store. She picked up the items she needed for the meal—“Meat,” Sam had told her with a shrug when she asked what Dean liked to eat, “and pie.”—as well as a bottle of wine and a case of beer for Sam and Dean.

By four o’clock she had the burgers cooking, the pie warming in the oven, and oil heating on the stove for fries. She uncorked the bottle of wine—a very sweet Moscato—as she congratulated herself on a passible, if carb-heavy dinner. She wasn’t the best cook, so…one source of anxiety down.

She had just begun to make a salad, the face that Sam would surely make when he saw the meal already clear in her mind, when she heard the apartment door open and close. She smiled and picked up her wine glass to head to the living room.

“Hey guys!” she called before raising her glass to take a drink.

Jess’ eyes landed on the man beside Dean just as she attempted to swallow the wine, and she wound up spitting it out instead. Not like in a movie, with a fine mist of liquid spraying out, but with a short puff of air that sent the liquid rushing from her mouth as she coughed.

She had been expecting Dean Winchester, Sam’s older brother.

The man who had walked into her apartment with her boyfriend instead was none other than Daniel Wesson.

Her face flamed red as she tried to control her coughing, her hand flying up to wipe at the wine that had flooded down her chin. “Sam, did you…” A coughing fit interrupted her and she tried again, looking from her boyfriend to the porn star and back again. “How…”

God, she was embarrassed. She couldn’t figure out how or why Sam had gotten her favorite porn star—and model for her favorite dildo—into their apartment, especially without talking to her first, but here she was, bright red, wine dribbled down her front, and unable to string together a full sentence without coughing.

“Uh…Jess, this is Dean.” Sam was looking at her with an expression that was half-concern, half-amusement. “Dean, this is Jess. My girlfriend.”

Daniel…Dean? It wasn’t humanly possible for two people to look that much alike. Well, twins, maybe, but surely Sam would have mentioned it if Dean had a twin, and one who worked in the porn industry, at that!

“Sorry,” Jess finally choked out. “Excuse me for a minute.”

“She seems nice.” Dean said as Jess made a quick exit to her and Sam’s room. “A little crazy, but all the best ones are.” He shrugged. “Boy, something smells good!”

“Yeah…” Sam muttered, staring after Jess and wondering what exactly had gotten into his girlfriend.

Jess, for her part, was having a hard time calming down. God, that had been embarrassing. It didn’t even really matter, in that context, whether the man Sam had brought home was Dean Winchester or Daniel Wesson; either way Jess had made the brilliant first impression of a choking moron.

She ran through the situation in her head, separating facts from guesses to try to make sense of the situation.

 **Fact** : Sam had said that he was bringing Dean over for dinner that night.   
**Fact** : Sam had actually introduced the man as his brother Dean. Explicitly.   
**Guess** : Sam wouldn’t suddenly change those plans, replace his brother with a porn star, and just waltz in. At least without calling first. So the man in the living room was probably Dean.

 **Fact** : Dean looked a _lot_ like Daniel Wesson.   
**Fact** : A lot of porn stars use pseudonyms.   
**Guess** : Dean likely _was_ Daniel Wesson.

 **Fact** : Sam had seemed completely unaware, both then and the night before, of who Daniel Wesson was.   
**Fact** : Sam had never told her exactly _what_ Dean does to pay for Sam to attend Stanford.   
**Guess** : Sam is likely completely unaware of the fact that his brother is a famous porn star. ‘

And following that…

 **Fact** : Dean has not told Sam what exactly he does to pay for Sam to attend Stanford.   
**Fact** : Dean has done this on purpose.   
**Guess** : Dean does not want Sam to know and Jess should not rat him out at the dinner table the first time they meet each other.

 _Oh sweet gravy._ Jess was so fucked. All of this meant that she would have to go out there and act normal as she ate dinner with the man who had, without his express knowledge, gotten her off at least three times in the last week alone.

 _Fuck_.

** ~~~ **

Sam and Dean were sitting on the couch—the couch where Jess had fucked herself with a replica of Dean’s dick just the day before… _twice_ —catching up over beer when she came back out of the bedroomroom, wearing a clean, dry shirt and considerably more composed than she had been when she left.

“You okay?” Sam stood up, coming close to her, eyes full of concern.

“Fine, fine.” She waved the concern off, blushing lightly. “Just got a bit embarrassed with the spit-take, is all. Sorry, Dean.” She turned her attention to the man on the couch, trying to take him in as Sam’s brother rather than Daniel Wesson, porn star and wet dream factory.

He looked (obviously) nothing like Jess had imagined him. He was shorter than Sam, a fact that was somehow at odds with the idea of him being the older brother, with short dirty blonde hair and piercing green eyes. He gave her a crooked smile, his permanently fucked-out lips twisting, and Jess felt her stomach flutter involuntarily. She had seen that look on his face more times than she could count, and it was as though her body were conditioned to react.

 _Great_. So now she was going to sit through dinner, making awkward small talk as she soaked her panties under the table. Awesome.

Dean’s smile widened as though he knew what he was doing to her. “No worries.” His voice was deep, rougher than Sam’s.

Jess forced herself to look away from that mouth, to ignore the voice issuing from it, and hurried back to the kitchen to start carrying out plates of food.

“I made hamburgers and fries. Nothing fancy, but it should taste good enough. Oh, and a salad.” She was talking now more to keep her mind occupied than anything. “There’s also pie for desert. Not homemade, but that’s probably for the best—”

“You got pie? For me?” Dean asked, looking taken aback.

Jess faltered for a second, as she set the plates down on the small table in the dining area. “Uh…yeah. Sam said you like pie…”

“Sammy, marry her.” Dean stood up, clapping Sam on the shoulder as he made his way toward Jess. “She doesn’t forget the pie!”

“I didn’t always forget the pie,” Sam grumbled, shaking his head, but a small smile spread over his face.

Dean rolled his eyes at Jess, back to Sam, and mouthed, “Always.”

Jess tried not to pay too much attention to those lips. She could tell this was going to be a problem every time the older Winchester spoke to her.

“Well…” She cleared her throat and sat down. “Dig in.”

Two bites into the burger, Jess heard Dean let out a low moan. She closed her eyes and took a calming breath as she felt her core clench in response.

“Damn, this is good.” The older brother wiped his mouth, catching Jess staring at him. “Sorry. Sammy says my table manners are _appalling_.” He said the last word in a snooty voice. “What can I say. I like to let myself enjoy what I eat.”

_Fuck that voice that can make fucking everything sound sexual._

“So how’s work going?” Sam asked, mercifully putting an end to the silence that had followed Dean’s last statement.

“Working my dick into the dirt.” Dean’s eyes flicked to Jess and _he fucking winked_. “Southern expression. Pardon me.”

Jess’ eyes flickered to Sam, who seemed unaffected by Dean’s words, or the wink. Was this just how Dean was? Or was he fucking with Jess? Was Sam in on it? Did Dean know that she knew; what he was doing to her? Did Sam?

_Fucking fuck could this dinner just be over already?_

But she hitched on the girlfriend smile, the one that said ‘I am in love with my boyfriend and I am definitely _not_ creaming my panties from the sound of your voice alone’, and asked, “What do you do? Sam’s never mentioned it.”

Sam looked surprised, as though just realizing something. “I never actually—”

“I work for a film studio in LA.” Dean flashed a calm smile at them.

Jess couldn’t read the expression on his face. She decided to prod harder. “Doing what?”

Dean narrowed his eyes, trying to read her in turn and coming up empty. “Mostly assistant stuff. Nothing _impressive_.”

“I beg to differ.” The words were muttered under her breath; she hadn’t actually even meant to say them, but in their close proximity around the small table the words sounded deafening. Sam was staring at her, confused. Dean was smirking at her as though she had just confirmed something he had suspected all along. Shit. She had to recover. “I just mean that it’s the people behind the scenes, the small jobs, that make or break a project.”

Sam seemed satisfied but Dean was still staring at her, that satisfied grin spreading across his face. “Maybe you’re familiar with some of the projects I’ve been involved in?”

“Nope. I don’t think so.” Jess stood up quickly, eager to stop Dean’s questions before they went too far. “I need another glass of wine.” She heard Sam excuse himself to go to the bathroom as she walked into the kitchen and pulled the wine from the fridge. She considered taking a long drink directly from the bottle, decided it would be unladylike, and instead poured a glass and downed it quickly before refilling it again.

She felt him come into the kitchen rather than hearing him. Before she knew it he was standing close to her back, so close that she could feel the heat from his body against the skin that wasn’t covered by her tank top.

When he spoke, his voice was quiet, barely a whisper. “You’ve seen it, haven’t you?”

She closed her eyes and nodded, flushing in unexpected shame. This was Sam’s _brother_ , for crying out loud.

There was another pause, and if she couldn’t still feel him she might have thought he had left. Then— “Does Sammy know?”

She shook her head and then jumped when she felt a strong hand on her hip. “Don’t tell him.” Dean’s voice was soft and pleading. “Please. He’ll lose his shit if he finds out; blame himself for it, cause of school.”

“I don’t know if—”

“ _Please_.” Dean’s mouth was practically touching her ear, the hard lines of his body pressed against her back. She couldn’t tell if he was just trying to be quiet or actually trying to seduce her. She heard a sharp inhale. “God, are you _wet_?”

Her face burned in shame again and she didn’t answer him. He let out a broken sort of laugh. “Well, if Sammy ever finds out, tell him I’m happy to join.”

Jess was saved from answering as they both heard the tell-tale rush of water in pipes from inside the walls, signaling that Sam was washing his hands and would be reappearing at any moment. Sure enough, when he appeared in the kitchen doorway moments later, Dean was cutting into the pie with a look of glee on his face and Jess was on her next glass of wine, her cheeks flushed, Sam thought, from the slight buzz she likely had by now.

** ~~~ **

The rest of the evening passed slowly for Jess. Every time Dean spoke her mind snapped back to the kitchen, to his body pressed against hers, his breath hot on her ear and cheek. She gave up on trying to quell the lust, especially with the knowing looks that Dean kept throwing her, and when it finally came time for the older Winchester to leave, Jess had to resist pushing him out of the door.

No sooner had the door shut, Dean officially gone from the apartment, than Jess was on Sam, pulling his head down to kiss him ferociously, her other hand busy pulling the bottom of his shirt up to fumble with his belt buckle.

“ _Shit_ , Jess… What’s gotten into you?” Sam sounded short of breath, confused but welcoming of this new decelopment.

Jess managed to tug his shirt off and pressed her body against his, placing a wet kiss on his chest. “Want you,” she muttered. “Please.”

“Fuck.” Sam seemed to be trying to get ahold of himself, regain control of the situation. “Wait, wait. I had an idea today.” He pulled Jess over to the couch and gently pushed her down.

She whined, the intense need for him redoubling. He was searching through the coffee table drawers, where they kept their DVD collection. “What are you looking for.”

“I want to watch that one porno you like.” He grinned devilishly at her. “Want to see you get off on it.”

Her stomach dropped so violently that she wouldn’t be surprised if she had actually turned green. Literally.

“Sam, wait—” Too late.

“Got it.” Sam pulled out the DVD case, his eyes glancing over the cover before doing a sort of double-take, the color draining from his face. “What the _fuck_?”


	3. Part Three

Sam was having some trouble coming to terms with the turn of events that had taken place in his life. First, he had watched his girlfriend—the girl he planned to _marry_ one day—fuck herself with a dildo modelled after a famous porn star. Then, he had fucked her with it, offered to use it to fuck her in the ass as he pounded her pussy. Then his brother Dean had visited, which had been awkward for reasons he hadn’t, at the time, been able to fathom.

And all of those instances he could get on board with if they were that simple. Hell, when he thought they were on simple his mind was doing a constant victory dance. He loved Jess, loved how fucking dirty she could be, all for him. And he loved his older brother, was psyched that he had finally come to visit after they had been separated for so long. Awkward or not, it had been great.

Until Sam discovered the source of the awkwardness.

Dean, his big brother, his childhood protector and his sponsor through college, was in fact Daniel Wesson, the porn star that Jess’ dildo was modeled after. Her _favorite_ porn star, and by extension the man who had likely gotten her off many, many times before Sam came along. It was enough to make Sam want to scream, to kick and throw a temper tantrum the likes of which hadn’t been seen since he was a kid and adamant that Dean _wasn’t playing fair_.

Here they were, adults. And Dean still wasn’t fucking playing fair.

Sam hadn’t spoken to his older brother in the three days that had passed since his visit and Sam’s discovery. Dean had called—twice—but Sam hadn’t picked up, hadn’t returned the call, hadn’t even shot off a lame-ass text message to his big brother.

He hadn’t talked to Jess much, either, but that was more because of her than any decision he had made to do so. Jess had been in and out of the apartment all weekend, only staying for brief periods of time before she needed to go to the library, or out to drinks with a friend.

Maybe she was fucking Dean.

Would it surprise him?

 _Yes._ It would honestly surprise him if Jess cheated on him with Dean. Just because…it was Jess. He knew her better than that.

That wasn’t to say that it hadn’t happened before. No, not Jess, never Jess. But there had been other girlfriends of his that had ended up under his big brother. His prom date, Rachel Nave, for example. On prom night, no less.

But Jess was different. He knew that. So why did his mind keep returning to that dark place?

_Maybe Jess is fucking Dean._

He couldn’t stop the thought from racing through his mind, no matter what he personally believed. The thought was there, like an itch deep under his skin. Once he was aware of it, he couldn’t get rid of it.

So that was why, when they were sitting on opposite ends of the couch two days later, bodies curled away from each other, Sam had to take the opportunity to ask, once and for all. “Are you fucking Dean?”

Jess’ head swung around to face him, a look of genuine shock on her face. Sam instantly felt guilty for asking. Had to, though. He had to know.

“No! Sam…” her voice was gentle as she unfolded her legs from under her and slid across the couch toward him, her hand coming to rest on his chest to brace herself as she swung a leg over his, leaning in to press light kisses to his cheek, his jaw, his lips. “Sam, I love you. I don’t want—”

She cut herself short and Sam almost laughed out of dark humor because fuck, he had to hand it to Jess, she wasn’t the lying type.

“You want to fuck him, though?” Why was Sam poking at it? Nothing about knowing could possibly make him happy.

“I was thinking…” Jess trailed off, licking her lips. “Dean said if you found out…that he’d be happy to… _join in_.”

Sam stared at her, trying to figure out where she was going with this. She didn’t speak again right away, and he made a sound in his throat to encourage her to continue.

“I have this…idea. A fantasy, I guess.” She squirmed a little in his lap and Sam both wished she’d hurry up and spit it out and that he had never opened this can of worms in the first place. She leaned closer, nipping up his jaw to his ear before taking the lobe in her mouth and biting down lightly, pulling at the tender flesh. “I want him to fuck me while you watch, Sam. Wanna know you’re watching it happen, hear your voice while he’s inside me.”

Sam turned that over in his head. A part of his mind rebelled at the thought of Dean touching Jess _at all_. Another part of him, and he couldn’t deny it, found the idea to be a huge, unexpected turn-on.

Encouraged by the lack of rejection toward the idea, Jess continued talking. “Wanna know it’s driving you crazy, watching your brother fucking me, making come on his dick, but that you can’t do anything about it. Then, when it’s over, I want you to take me, show me who I _really_ belong to. _Own me_. Make me come harder than he ever could.”

Sam had to let out a low moan at that; couldn’t help it. The idea was taking root in his mind, as securely as if he had thought of it himself.

“Please, Sam?” Jess breathed against his mouth. “Won’t do it if you don’t want to.”

“One condition,” Sam said, a smirk twisting his lips as the idea clicked into place. Jess squirmed in his lap again, eager to hear what he had come up with. “You have to let Dean fuck you with that dildo up your ass. Let me watch as he takes _both_ holes.”

“God, Sam…”

“And…” Sam let the word hang in the air for a minute, relishing the way she writhed in anticipation, nearly getting off on the idea alone. “That’s all you get. After that, I’m gonna keep you on the edge, keep you begging me—only me—to fuck you. You won’t get to come until I decide you can. Might be hours…might be _days_.”

God, he hoped she’d say yes. And of course she did, nodding her head in agreement almost immediately.

“Need you now, though,” she moaned, her face buried in his neck as she ground down on his hardening length.

Sam gave her a predatory grin and stood, picking her up with him, and took her to their bedroom.

** ~~~ **

The other end of the line was quiet, and if he couldn’t hear the faint crackle of a live line Sam would’ve thought that Dean had hung up on him. He waited patiently as he imagined his older brother—normally so confident and in-control—struggling to form words.

“Fuck, Sammy.” That was all he got, uttered on an exhale.

“So what do you think?”

He heard the sharp inhale and slow exhale, tell-tale signs that Dean was smoking on the other end. Sam was a little disappointed the other man hadn’t quit after all these years.

“Fuck, Sammy,” Dean said again. “I’m just trying to wrap my head around it, you know? Thought you’d be pissed as hell when you found out what I do, but instead you’re calling me asking me to fuck your girlfriend?”

“Jess said you’d offered.” Sam shrugged even though Dean couldn’t see him.

The line was quiet again for a moment before Dean spoke. “Wouldn’t turn it down, nah. And I gotta admit, I like this plan a lot better than you being involved—no offense, baby boy.”

“Don’t call me that when we’re planning how to fuck my girlfriend together. It’s weird.” Sam rolled his eyes.

“Yeah, _that’s_ the weird part.” That sharp inhale, slow exhale again. “Yeah, I’ll do it. Sure you can handle it, Sammy?”

“Why couldn’t I?”

“Well, apparently your girlfriend’s already a huge fan of my dick, and she’s never even really had it. Risky, isn’t it?”

Dean was teasing him, just fucking around, and Sam knew it, but it still ruffled his feathers, so to speak. “I really doubt I have anything to worry about.”

“Suit yourself.” Sam could imagine Dean shrugging on the other end of the line. “Friday night, then?”

“Yeah.”

Two days away. In just two days, Sam would be watching his girlfriend get fucked by his older brother.

He smirked. And for three days after that, she’d be begging him to do the same.

** ~~~ **

The awkwardness didn’t set in until about a half-hour before Dean was scheduled to arrive at their apartment. It occurred to both Sam and Jess that they had no idea how this was supposed to start, only the eventual result. Dean was lucky, Sam thought. He had to have played out a hundred scenes like this on camera, the openings scripted for him. For Dean, this would be nothing. For Sam, it was a nerve-wracking awkward wait.

At exactly nine o’clock there was a knock at the door. Sam and Jess locked eyes, each looking at the other expectantly. Sam spread his hands in a wide gesture, shrugging slightly as if to say, what? I’m not involved in this.

So it was Jess who answered the door, and they both realized quickly that they didn’t need to worry about lines, or setting up a scene, because the second the door was open Dean was on Jess, his hands coming up to her face and holding her head steady as he kissed her passionately, walking her backward and then kicking the door shut behind them. He pushed her up against the wall, his body covering hers and his hands leaving her face to travel down to her hips, pulling at the hem of her tank top and yanking it over her head before returning his mouth to hers, plunging and pillaging with his tongue, thoroughly ravishing her.

It was happening a lot faster than Sam thought, and he felt jealousy rising up in his chest as Dean trailed one hand down Jess’ thigh, hitching her leg up to wrap around his hips, creating a better angle to thrust his denim-covered length against her soaked center.

As though Dean could sense Sam’s envy, he pulled his mouth away from Jess’ and looked over his shoulder, eyes dark and that shit-eating grin on his face as Jess gasped and rubbed herself against him. “Remember, Sammy, you’re just watching tonight.”

Sam nearly bit through his tongue.

Dean brought one hand behind Jess’ back and made quick work of the clasp on her bra, pulling his upper body away from hers to pull it off of her shoulders and toss it over his own, towards Sam. Jess’ hands were pulling at his shirt, desperate for the feel of skin-on-skin, and he quickly ridded himself of that, too.

He hoisted her up, guiding her legs to wrap around him before gripping her ass and moving away from the wall to carry her to the bedroom. This took Sam by surprise. He hadn’t imagined this taking place in their bed— _his_ bed. But he followed them anyway, and took a seat in the chair by their closet, the one that had until that point served no real purpose other than to—as Jess put it—tie the room together. Well, now it was the chair that he would sit in to watch his brother fuck his girlfriend.

He watched as Dean flipped her over onto her stomach, felt slight relief that Dean was going to do it that way, keep it impersonal. From his seat he had a view of the two of them from the side, and he focused on Jess, doing his best to cut Dean out of his vision as he stripped her and then himself of their pants and underwear.

“Fuck, no wonder Sammy’s so possessive of you.” Dean’s voice was a low growl and it surprised Sam what hearing his brother’s fucked-out voice did to him when it was coupled with Jess’ broken gasps and moans. His brother’s hand was smoothing down Jess’ back, finally reaching the cleft of her ass and then grazing further to dip into her pussy. “So fucking hot. I wouldn’t want to share you, either.” He fucked her slowly with his fingers, and Sam imagined that it was him doing it. “How’d you do it, huh? How’d you convince him? You wait until he was deep in your tight cunt, about to come, and then ask him to let his brother fuck you? You convince him with your pussy?” Dean let out a choked groan and Sam knew from the sounds that Jess was making that she had just gotten impossibly wetter, tighter, hotter around his fingers. “God, what a fucking slut.”

And Sam should be mad that Dean was talking to his girlfriend that way. But he knew what it did for Jess, how worked up she got, and Sam imagined that his filthy mouth was probably one of the reasons that he was one of her favorites. He felt himself getting hard despite his initial jealousy, which was quickly making way for an inferno of lust.

Dean’s fingers were pulling out of her pussy now, gliding up towards her ass and the tight pucker nestled between the perfect globes of her ass. “He ever fuck you here? You ever let him slide in, fuck your ass until he comes? Or is that just for when you think about me, fucking those other girls? You slide that fake dick in here, imagining it’s me.”

Jess didn’t answer, her voice already too fucked-out to respond. Dean smirked and teased one finger into her ass. “Mmm…maybe I’m wrong. Maybe you’ve never had anything in here.”

Sam smirked. He had been there. His cock gave a painful throb at the memory.

He watched his brother work Jess open, starting with a single finger and ending with three before he withdrew, leaning over her to open the bedside drawer. He came back with the dildo and a condom. It occurred to Sam that he and Jess hadn’t used condoms in a long time, not since moving in together, and Sam had no fucking idea how old the ones in the drawer were. But he knew they were good for a long time, and they had only been in the apartment six months, and lust was clouding his mind as his brother slid the dildo into Jess’ pussy, letting her fuck herself on it, covering it in her slick fluids, and then moved to slide it slowly into her ass.

Jess let out a scream that was half-pleasure, half-pain, her nails digging into the bed under her as she was filled to bursting.

Dean swore quietly. “Shit, baby. You sure you’re going to be able to handle all of this?” His voice was taunting, but Sam could hear the underlying concern in his brother’s voice.

Sam took a second to unstick his throat and find his voice. “She can take it.” His eyes met Jess’ as her head turned to look at him, a flush rising in her cheeks. “Can’t you, baby? That’s right. You can take it all; can take anything he has to give you.” He smirked at his brother. “I’m bigger, after all.”

Dean let out a harsh laugh. “Well, fuck. You’re fucking trooper of the year then, aren’t you, you fucking cockslut?”

Jess let out a moan and spread her legs wider. Sam felt a strange surge of pride as he watched her prepare to take Dean in. _Atta girl_ , his brain screamed.

“Please, Dean…” They were the first words Jess had managed to force past her fucked-out vocal cords. “Need you…”

Dean swore loudly before ripping the condom open with his teeth and rolling it on over his straining dick. He shifted forward a bit on his knees, gripping Jess’ hips to hold her steady, and then he was slamming into her.

Jess screamed, arching against him, mind blown from the completely full feeling of Dean’s dick in her ass and her pussy. Dean let out something like a feral growl. “Fuck…so fucking tight…so fucking hot. _Fuck_ , baby.”

His brother was thrusting in and out of Jess now, a steady, punishing pace, and Sam unzipped his pants, easing them down, along with his boxers, over his straining dick and halfway down his thighs. He gripped his cock, pulling hard, in time with his brother’s thrusts, imagining himself in Dean’s place.

“Fuck, baby, you’re doing so fucking good,” Sam gasped, watching Jess take it all, her face a mask of complete pleasure. “Hope you take it that good for me.”

Jess let out a desperate sob at his words and Dean swore again and picked up the pace.

“Fuckin’… Keep talking to her, Sammy. She gets so fucking wet when you talk.”

Sam felt his chest swell with possessive pride. “Gonna have you begging for it, Jess. Gonna let you get so close to what you want, and then send you on to class. That what you want? A plug in your ass and one of those little vibrators in your pussy? Make you keep it in all day, forbid you to come. Make you wait until you’re with me, until I say you can. Can you do that for me, baby? Can you stop yourself from coming like the cockslut you are? Wait for me to give it to you? I’ll have you begging for it, Jess, and fuck I’ll make it so good.”

“Please,” Jess choked out, pushing back against Dean’s brutal assault, feeling the two dicks slide against each other with only a thin membrane of tissue separating them. “Please, Sam. Let me come, please!”

“Go ahead, baby. Dean’s got you. Come all over his dick.” Sam smirked as Dean let out a startled cry and then one last loud curse as Jess came around him, milking him, making him shoot his own load. Sam worked his dick faster, chasing his own orgasm, and came soon after.

Fuck, he hated to admit it, but Jess had some fucking fantastic ideas.

  
**The End.** _I hope you enjoyed it. :)_  



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